Moving to Westchester: Best Towns for Families in 2025
Why Families Choose Westchester
Westchester County offers a rare balance: proximity to New York City with space to grow, exceptional schools, and distinct community identities. Families move here for safety, education, and access to walkable downtowns, while still enjoying suburban privacy and green space. For families transitioning from the West Coast or urban environments, Westchester can feel both grounded and aspirational.
Inside Westchester: School Districts, Commutes & Taxes
Westchester’s geography divides roughly into three zones: southern (closest to NYC), central, and northern. Commute times vary accordingly. Southern towns like Larchmont, Scarsdale, and Dobbs Ferry offer express Metro-North access and shorter city commutes. Northern towns like Yorktown Heights or Katonah may trade longer drives or train rides for more land and lower cost per square foot.
School district performance varies, but most Westchester districts rank well above state and national averages. However, logistics matter. Pleasantville, for instance, has no school bussing. Pocantico Hills offers only K-8; students must transfer districts for high school. Taxes differ significantly by town and district. Some towns, like Hawthorne, have lower taxes but fewer public amenities.
Westchester Towns and Villages: Personality & Fit
Pleasantville
- Reputation: Highly walkable, inclusive, and education-focused
- Schools: Excellent, though no bussing
- Politics: Generally liberal
- Vibe: Downtown community with arts and strong parent engagement
- Housing: Competitive pricing, especially post-COVID
Hawthorne / Thornwood / Valhalla (Mt. Pleasant area)
- Reputation: Quiet, suburban, politically conservative
- Schools: Solid performance; Mt. Pleasant district
- Commute: Express train from Hawthorne
- Vibe: Small-town feel; family-oriented
- Notes: Increasingly competitive market
Pocantico Hills
- Reputation: Small and close-knit
- Schools: K-8; choice of high school (e.g., Briarcliff, Pleasantville, Sleepy Hollow)
- Vibe: Rural charm with proximity to Pleasantville amenities
- Housing: Limited inventory; specific appeal
Yorktown Heights
- Reputation: Family-oriented, more space for the money
- Schools: Two districts; generally strong reputation
- Commute: No direct train line
- Vibe: Suburban with rural elements; changing demographics
Larchmont, Mamaroneck, Rye (Sound Shore)
- Reputation: Waterfront, affluent, family-friendly
- Schools: Top-tier
- Commute: Strong Metro-North access
- Vibe: West Coast-like in community structure and walkability
Northern Towns: Katonah, Chappaqua, Somers
- Reputation: Elite schools, spacious living
- Commute: Longer, but feasible
- Vibe: Idyllic, outdoors-focused; high quality of life
Westchester According to Locals: Community Insights
A wide range of experiences emerge from recent movers:
- Pleasantville stands out as both walkable and welcoming, particularly for families with children in arts or special education
- Hawthorne and Thornwood are seen as politically conservative, which may be a consideration depending on family values
- Yorktown offers space and affordability, but lacks walkability and has no train access
- Pocantico Hills offers charm, but its lack of high school creates a transition point for students
- Pricing pressure is real: homes that once sold for $600k pre-COVID now list over $800k to $1.4M in popular towns
Things to Consider Before Choosing a Town in Westchester
Use this decision framework:
- Do you need a walkable downtown?
- Is a strong public school district essential, including bussing?
- How critical is a short NYC commute?
- Are you looking for political alignment or diversity?
- What’s your long-term budget for taxes and home equity growth?
- Do you want a vibrant cultural community, outdoor access, or both?
What Type of Town Fits You?
The Commuter Couple with Kids
- Priorities: Fast train, walkability, excellent schools
- Fit: Pleasantville, Dobbs Ferry, Larchmont
The Outdoorsy Young Family
- Priorities: Land, trails, open space, good schools
- Fit: Katonah, Bedford, Yorktown Heights
The Value-Oriented Investor
- Priorities: Property value appreciation, space, emerging markets
- Fit: Yorktown, Thornwood, Valhalla
How to Explore Westchester Before You Buy
Spend meaningful time in target towns:
- Visit local parks, playgrounds, and grocery stores
- Attend open houses and talk with realtors
- Observe who uses the library, rec center, and train station
- Check school calendars and parent organizations
- Review real estate listing volume and turnover trends
Joining town-specific Facebook groups is also a powerful way to understand tone, culture, and common concerns.
Long-Term Considerations
Westchester isn’t just about the next 3–5 years. Your town becomes your community: friends, schools, civic engagement, even values. Choosing wisely means securing not just a property but a lifestyle and future network for your family.
As prices rise and neighborhoods evolve, many families find that choosing a town with growing demand, engaged residents, and strong school systems offers both emotional and financial returns.
FAQs About Moving to Westchester
Does Pleasantville really not offer school bussing?
Correct. All students walk, are driven, or arrange alternative transport.
Which towns are best for commuting to NYC?
Hawthorne (express train), Pleasantville, Larchmont, Scarsdale, and Dobbs Ferry are top choices.
What towns lean more politically conservative?
Yorktown, Thornwood, Hawthorne are mentioned as red-leaning within a largely blue county.
Where can I find more affordable housing with good schools?
Yorktown and Valhalla currently offer more value relative to Pleasantville, Chappaqua, or Larchmont.
Is Pocantico Hills a full K-12 district?
No. It offers K–8, and students then select a high school in a neighboring district.
Next Steps
If you’re planning a move to Westchester, download our free town comparison guide or schedule a strategy call with a local advisor. We’ll help you protect your lifestyle and connect you with local partners to make the move a breeze.